Highland Beach Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Highland Beach

Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,793 reviews)
"We stayed at Governor Calvert's House. The location is excellent for walking around downtown and the staff were very friendly and helpful."

Reviewed on 2 Jul, 2025

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Historic Inns of Annapolis
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is S$225 per night from 27 Jul to 28 Jul
S$225
27 Jul - 28 Jul
includes taxes & fees
9.4/10 Exceptional! (1,011 reviews)
"We enjoyed our stay. Friendly. Comfortable. Parking is pricey."

Reviewed on 28 Jun, 2025

Graduate by Hilton Annapolis
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is S$143 per night from 4 Aug to 5 Aug
S$143
4 Aug - 5 Aug
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"walking distance to shopping, quiet, clean and safe."

Reviewed on 2 Jul, 2025

Hilton Garden Inn Annapolis Downtown
See all 1,208 properties in Highland Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

What to do in Highland Beach

Food Tour Plate

Historic Annapolis Food Tour

S$102
per adult
Historic Annapolis Food Tour
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

S$13
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Annapolis: Ghosts of the Harbor & Old Town Tour

Apparitions of Annapolis Ghost Tours: Ashes to Agony

S$35
per adult
Apparitions of Annapolis Ghost Tours: Ashes to Agony
See all activities in Highland Beach

Frequently asked questions

How much does a Highland Beach holiday package cost?
You'll find cheap prices on Expedia for your Highland Beach escape. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Highland Beach costs.
What are the cheapest months to go to Highland Beach?
You can typically find lower prices and better availability in January, February and March. Explore our cheap Highland Beach holiday packages and you could land some excellent off-season deals.
How many days is enough for Highland Beach?
The ideal duration for your Highland Beach holiday depends on what you'd like to do. Typically, a few days to a week will give you time to visit all the leading sights and discover some hidden treasures along the way.
How to find the best Highland Beach package deals?
Use Expedia's handy filters to help you find some tempting Highland Beach package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Highland Beach package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as soon as possible.
Is it cheaper to book a Highland Beach holiday as a package?
You can enjoy significant savings on your next Highland Beach retreat by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Highland Beach?
Land amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Highland Beach break.
How to plan a trip to Highland Beach?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Highland Beach.
  2. Set a budget: Consider expenses like flights, transportation and food when calculating how much to save for your trip to Highland Beach. Then, select a property that matches your budget, whether that's an economical option or a lavish getaway.
  3. Decide your trip length: Think about how long you want to spend exploring Highland Beach. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your airfare and accommodation: Once you've nailed down your dates and duration, lock in the right Highland Beach holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.